


An Average Day in the Life of Dean Winchester... Now with More Pie!

by MugenYumeDansu



Category: Supernatural
Genre: Alternate Universe - Canon Divergence, Anal, Blowjobs, Bottom!Gabriel, Dean gets Laid!, Dean is caught off guard, Dean loves his pie, Flirting, Gabriel is a smooth operator, Gabriel is a waiter, Hothothotness, M/M, Normal Life, Pie Is Awesome, Sexy Times, Smut, gabriel is sexy, top!dean
Language: English
Status: Completed
Published: 2014-09-14
Updated: 2015-02-27
Packaged: 2018-02-17 10:00:47
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 2,216
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2305703
Author URL: https://archiveofourown.org/users/MugenYumeDansu/pseuds/MugenYumeDansu
Summary: <blockquote class="userstuff">
              <p>Dean + Pie = Happy<br/>Dean + Gabriel = More Happy</p><p>Or the one where Dean goes to his favorite restaurant and orders his usual. And gets to take the gorgeous waiter home.</p>
            </blockquote>





	1. Chapter 1

Dean pulled his '67 Impala into the parking lot of Jay Bird's Diner and cut the engine. He patted Baby's dash and stepped out, heading into his favorite place to grab a bite.

The little bell above the door jingled merrily, announcing his entrance. He strolled over to his favorite table and sat down. He didn't bother checking the menu, he already knew what he wanted. The same thing he got every saturday morning.

He waited patiently for Cindy, the waitress to come around. Glancing out the window, he noted the slight gray tint to the clouds. It was probably going to rain later in the evening, or early the next morning.

Dean was drawn out of his musings by someone clearing their throat. Dean looked up at Cindy, a witty line already in his lips...

Only to stall as his eyes met a pair of bright golden orbs instead of pale blue ones. Dean blinked and took in the face of the person standing there. Light brown hair slicked back from an aquilian face, straight nose, cupid's bow lips, high cheekbones, and the most striking golden brown eyes Dean had ever seen. He was speechless.

  
"Would you like to order, or not?" The beautiful creature asked, in a very annoyed tone, but the voice was a soft timbre. The sound went straight to Dean's groin in a swift rush of blood.

"Uh... Yeah, yeah. I want the double bacon cheeseburger, side of cheese fries, large iced tea, and two slices of pie, one pecan, one blackberry." Deans rattled off his customary order. He glanced at the guy's nametag as he scribbled down the order. Gabriel, it read.

"That all?" Gabriel asked, dropping the irritated demeanor. Dean nodded. Gabriel smiled, all cocky charm, turned and walked away to log Deans order in queue.

Dean watched him go, noticing that Gabriel wasn't much more than 5'5". He also had a swagger to his walk, and a very nice ass.

  
Dean's interest was piqued.


	2. Chapter 2

Speculations and planning kept Dean busy while he waited for his food to arrive. He also watched his golden eyed waiter flit from one table to the next, taking orders and doing his best to keep a smile on his gorgeously sculpted face. His tea had already been delivered, and he sipped idly on it as he thought.

Cindy made an appearance at one point, poking her head out the kitchen door and waving at dean, all smiles and bouncy hair. Apparently she was filling in for the cook.

Dean felt a little grateful to this turn of luck. He wouldn't have had a chance to oggle this adorable ass, or any other of Gabriel's assets otherwise. And assets they were...

Deans reordered his thoughts when the object of them came striding toward him with an arm full of plates.

"There you go." Gabriel chimed pleasantly, settling Dean's meal in front of him. He smiled and it lit up his whole face. Dean nearly lost his breath. Gabriel was absolutely stunning.

"Can I get you anything else?" The waiter asked. Dean considered replying 'Your number' but kept that to himself.

"Yeah, some whipped cream for my pie?" Dean asked.

"Whipped cream, huh?" Gabriel asked, raising an arched eyebrow. The smirk painted across that elegant face made Dean blush. Gabriel turned with an amused half smile.

"Be right back with that." And he actually winked before walking briskly away. Dean shifted, trying to get comfortable in his now too tight jeans.

Dean was halfway through his burger when Gabriel breezed by, leaving a bowl overflowing with the fluffy white treat, and a generous spoonful of glazed cherries as well. He winked again and flitted off to the next table, the next order.

When Dean finished his meal, and his dessert, and went to pay, he dropped a little more than his customary three dollar tip on the table. Gabriel met him at the register, smile plastered across his face.

"Enjoy your meal?" Gabriel asked after he'd wrung up the ticket.

"Yes I did. Nice touch, by the way." Dean answered, handing over the money.

"Why, whatever do you mean? I was only doing my job." Gabriel's eyes glinted mischievously.

"You did it very well, Gabe, can I call you Gabe?" Dean attempted to go the usual pick-up path. When Gabriel nodded Dean flashed his most dazzling smile and accepted the change the waiter handed him. "So, uh, when do you get off?"

"You mean off my shift, or something far less innocent?" The blonde asked. Dean was more than a little surprised at that. Before he could respond Gabriel had handed him the receipt.

"How about tonight, around sixish." And he turned to go back to what he was supposed to be doing.

"Wait, can I get your number?" Dean blurted out.

"You already have it." Gabriel replied, a cocky lilt in his tone. Bewildered, Dean glanced at the piece of paper clutched in his hand. There across the bottom was a series of numbers.

Smiling Dean turned and headed out to his car.


	3. Finally!

**Summary for the Chapter:**

> I'm just gonna skip right to it. This is what everyone wants anyway.

**Notes for the Chapter:**

> Incomplete!! Most of my chapter got deleted by accident right before posting. I will fix it later, sorry! Until then its a split chap, Chapter 4 is the rest.

Dean paced a little nervously around his motel room. He was waiting for that knock at the door signalling Gabriel's arrival.

He had called the number that the waiter had left him about an hour ago. Gabriel had answered on the second ring. He had then asked when, and where. Dean had told him. Now he was playing the waiting game.

He'd dressed up nice, in a dark blue button up over a pristine white tank, his nicest jeans, and he'd even cleaned his boots and styled his hair. All in hopes that Gabriel liked what he saw when he finally arrived.

The knock startled Dean, and he almost tripped in his haste to get the door. He paused with his hand on the doorknob, taking a deep breath and attempting to calm his nerves.

He turned the knob and swung the door open almost casually. Gabriel stood there in a nice amber colored shirt, black slacks, hair slicked back, hands in his pockets. He had that adorable half-smile on his face again, eyes twinkling.

"Gonna invite me in, or just stare at me all night Dean-o?" Gabriel asked, raising a well sculpted eyebrow. Dean stepped back and motioned the shorter man in.


	4. Finally! Part 2

Gabriel moved past Dean into the room, not even bothering to look like he hadn't done this kind of thing before.

Dean shut the door, closing them in together. He turned the lock and stepped toward Gabriel.

The golden eyed man turned to him, amused.

"How you wanna do this? You topping or me?" He asked nonchalantly. Dean actually blushed.

"Well, me I guess." He replied. No sooner than that Gabriel started unbuttoning his shirt. He dumped the shirt over the back of a chair and moved forward until the two men's faces were mere inches apart. Dean licked his lips, looking from Gabriel's eyes to his lips and trailing down his toned chest. Gabriel smirked. Heat pooled low in Deans belly. He felt himself stir.

Dean leaned in, crossing the distance between them and brushed his lips over Gabriel's. The other man reacted immed iately, lips moving to meet Dean's every move. Dean deepened the kiss, arms coming up around Gabriel's bare back, drawing him in. Gabriel opened his mouth to Dean, taking it a step further.

Before either was aware their tongues were fighting for dominance and Gabriel had fisted his hands in Deans shirt. They ground against each other, erections coming awake and to full attention in moments.

Dean groaned and stepped into Gabriel, pushing him back towards the bed. He'd lost all hint of nervousness with the start of the kiss. The sparks were flying between the two men like the fourth of July.

Dean backed Gabriel up until the backs of his knees met the edge of the bed. They toppled over, still locked at the lips, tongues dancing, teeth clicking together, lips moving in tandem. They bounced lightly, but it didn't hinder them.

Gabriel's hands slipped under Dean's shirt and found a sensitive nipple, scraping across it lightly. Dean shuddered and broke the kiss for a moment. They were both breathing hard, flushed and just beginning to break out in a light sweat.

Dean became aware of his erection, straining against his zipper and painfully hard. He needed to get naked. Now. He reared up and began fumbling at the buttons of his shirt. Gabriel started on them too, finally getting it undone and pushed off his shoulders. The white undershirt came over his head and went flying across the room. Next his zipper was down and his pants were being pushed down by both of them. When Dean was free of all but his boxers he went to work on Gabriel's pants. The two men were in nothing but their underwear and grinding against one another in seconds. Dean's lips crashed down on Gabriel's once more.

Gabriel's hands went to work pulling at Dean's boxers. The smaller man's hand slipped inside and wrapped around Dean's cock, pumping him slowly. Dean groaned and ground into his grip. Gabriel caught Dean's lower lip between his teeth and sucked on it. Dean felt a rush of precum dribble down his cock and Gabriel's fingers as he nearly saw stars.

Dean dragged his nails down the sensitive flesh of Gabriel's side, causing the golden haired man to whimper and gasp. He thrust up into Dean as he flung his head back.

"Oh, God Dean, please!" He cried in a hoarse voice. Dean needed no more than that, he moved down and practically tore Gabriel's boxers down, taking the thick length into his mouth. Gabriel keened, fucking into the hot wetness.

Dean sucked hard before letting Gabriel's member slide free with an audible pop. He reached over to the bedside table and grabbed the lube he'd stashed there earlier. He coated two fingers in the thick substance and tossed the bottle on the bed. He lifted one of Gabriel's legs and circled the tight pucker there with his fingers.

"Ngh!" Gabriel almost came off the bed when his hips snapped up. Dean pushed his hips down and slowly slid a lubed finger into the smaller man. Gabriel was very vocal about how much he liked that. Dean twisted and slid his finger in and out until Gabriel loosened up some, all the while exploring the other's neck and chest with lips, tongue and teeth.

Gabriel tightened his grip on Dean's side, hair, or wherever it happened to be when Dean got a particularly touchy spot. Gabriel's hands roamed, rubbing, scratching, and digging in at times. Gabriel's mouth wasn't idle either, he kissed and nipped at Dean's neck and chest while the bigger man's fingers fucked him open. He hissed and bit down on Dean's collarbone when a third finger joined the other two.

Waves of pleasure washed over him, bringing him closer and closer to the edge. Before it got too far Dean pulled his fingers out of the other man. Gabriel whimpered at the emptiness inside him. Then Dean's cock was nudging his entrance and Gabriel moaned loudly and squirmed, it felt so good.

"Ready?" Dean asked. Gabriel nodded and Dean slid into the tight heat slowly. When he was fully impaled he stopped, letting themm both adjust before he began thrusting.

On the fourth thrust Dean hit Gabriel's prostate, and suddenly Gabriel's was keening again and digging his heels into Dean's ass, arching off the bed.

Dean almost came at the feeling of Gabriel clenching around him and shifting his hips from side to side. Dean's hands went to Gabriel's hips and he sat back on his calves, pulling the other into his lap. He thrust hard, hitting the sweet spot again. Gabriel went mindless, rocking his hips and fucking himself on Dean's erection with each thrust.

Dean thrust hard, balls slapping Gabriel's ass with each thrust. He was pounding into the other man mercilessly, hitting his prostate every time. Suddenly Gabriel siezed up, shouting, and came hard all over both of their bellies and chests. Dean followed close after him as the clenching around him forced him over the edge. He rocked into the blonde twice more before coming so hard he saw nothing but white for several seconds.

Dean pulled his softened cock out of Gabriel's ass and flopped down beside him, breathing hard and covered in sweat and cum.  
Gabriel lay with one arm over his eyes, and one leg bent, breathing just as hard.

"That. Was. Fucking incredible." Dean said after he caught his breath some.

"Hell yes." Gabriel agreed, peeking out from under his arm and grinning. "Never come that hard before in my life."

"Me either." Dean admitted. A wave of exhaustion settled over him. he rolled on his side and flung an arm over Gabriel's middle. He didn't care that he was laying in the other's bodily fluids. He just wanted to sleep. Gabriel must have agreed, as the gorgeous man snuggled into Dean's side, pulled the rucked up blanket over them both, and settled.

They were both tucked into each other close, and completely out in minutes. And that is how they slept all night; wrapped in one another's arms, perfectly content to stay right there.

**Notes for the Chapter:**

> Aw, a little bit of fluff at the end. Couldn't resist, haha!
> 
> Anyway this is complete.  
> ...  
> Gasp! My first complete multi-chapter story! My god I thought it would never happen, but here it is. I'm extremely proud of myself!
> 
> Thanks for reading! And for all the enthusiasm, and the many kudos. It means a lot to me yall.
> 
> Now I go work on my other multi-chap stories.  
> Love yall!


End file.
